JP2007505873A5 - - Google Patents
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- JP2007505873A5 JP2007505873A5 JP2006526684A JP2006526684A JP2007505873A5 JP 2007505873 A5 JP2007505873 A5 JP 2007505873A5 JP 2006526684 A JP2006526684 A JP 2006526684A JP 2006526684 A JP2006526684 A JP 2006526684A JP 2007505873 A5 JP2007505873 A5 JP 2007505873A5
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- JP
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- Prior art keywords
- alkyl
- formula
- group
- oxy
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000217 alkyl group Chemical group 0.000 claims 133
- 150000003246 quinazolines Chemical class 0.000 claims 45
- -1 hydroxy, cyano, amino, carboxy, carbamoyl Chemical group 0.000 claims 41
- 125000003545 alkoxy group Chemical group 0.000 claims 37
- 125000001424 substituent group Chemical group 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- 229910052757 nitrogen Inorganic materials 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- 125000003282 alkyl amino group Chemical group 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 16
- 125000000524 functional group Chemical group 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000005236 alkanoylamino group Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- 125000001589 carboacyl group Chemical group 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 125000004423 acyloxy group Chemical group 0.000 claims 7
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 6
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 238000003780 insertion Methods 0.000 claims 4
- 230000037431 insertion Effects 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 3
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- 230000001028 anti-proliverative effect Effects 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims 2
- PGHNHXUHPOOBFU-QFIPXVFZSA-N 1-[(2s)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@H]1COC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 PGHNHXUHPOOBFU-QFIPXVFZSA-N 0.000 claims 1
- DBTFQRQGEVHZRH-FQEVSTJZSA-N 1-[(2s)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC[C@H]1COC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 DBTFQRQGEVHZRH-FQEVSTJZSA-N 0.000 claims 1
- OBYKUWKNPXQDFJ-QHCPKHFHSA-N 1-[(3s)-3-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1N(C(=O)CN(C)C)CCC[C@@H]1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 OBYKUWKNPXQDFJ-QHCPKHFHSA-N 0.000 claims 1
- LTPJXGTYIXMFCA-NRFANRHFSA-N 1-[(3s)-3-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-hydroxyethanone Chemical compound C1N(C(=O)CO)CCC[C@@H]1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 LTPJXGTYIXMFCA-NRFANRHFSA-N 0.000 claims 1
- MTILJCKKYKSSDN-FQEVSTJZSA-N 1-[(3s)-3-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypyrrolidin-1-yl]-2-hydroxyethanone Chemical compound C1N(C(=O)CO)CC[C@@H]1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 MTILJCKKYKSSDN-FQEVSTJZSA-N 0.000 claims 1
- JGVZYQZWYSNTCH-UHFFFAOYSA-N 1-[3-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxyazetidin-1-yl]-2-hydroxyethanone Chemical compound C1N(C(=O)CO)CC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 JGVZYQZWYSNTCH-UHFFFAOYSA-N 0.000 claims 1
- CZSCWJRJMFZFKN-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 CZSCWJRJMFZFKN-UHFFFAOYSA-N 0.000 claims 1
- WGQGZSZZIHOYIG-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(C)=O)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 WGQGZSZZIHOYIG-UHFFFAOYSA-N 0.000 claims 1
- HHNVLCSQZBHLNB-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)C2=C1 HHNVLCSQZBHLNB-UHFFFAOYSA-N 0.000 claims 1
- WGXUEMXKOANYOP-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)C2=C1 WGXUEMXKOANYOP-UHFFFAOYSA-N 0.000 claims 1
- REHCWAJWIQRJSL-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)C2=C1 REHCWAJWIQRJSL-UHFFFAOYSA-N 0.000 claims 1
- YXDCDWQQOISSGA-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 YXDCDWQQOISSGA-UHFFFAOYSA-N 0.000 claims 1
- PWYDEQIFZMVYET-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-hydroxyethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CO)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 PWYDEQIFZMVYET-UHFFFAOYSA-N 0.000 claims 1
- DLTYTEJYAVHQND-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(C)=O)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DLTYTEJYAVHQND-UHFFFAOYSA-N 0.000 claims 1
- ZTLIKJIKMQGZPP-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 ZTLIKJIKMQGZPP-UHFFFAOYSA-N 0.000 claims 1
- CONRNKRWLJGEOF-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 CONRNKRWLJGEOF-UHFFFAOYSA-N 0.000 claims 1
- TVTCNDDTASWGPG-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 TVTCNDDTASWGPG-UHFFFAOYSA-N 0.000 claims 1
- DTJKKDWPYCFBJL-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical class C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 DTJKKDWPYCFBJL-UHFFFAOYSA-N 0.000 claims 1
- HZXMBZJCQBUOES-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 HZXMBZJCQBUOES-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- ZASCFESQWRTKCG-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[3-methoxy-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=NC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(C(=O)CN(C)C)CC1 ZASCFESQWRTKCG-UHFFFAOYSA-N 0.000 claims 1
- UPBAVUPJRVMCCR-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[3-methoxy-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(C(=O)CN(C)C)CC1 UPBAVUPJRVMCCR-UHFFFAOYSA-N 0.000 claims 1
- GWVYGWZSKXFUDP-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=CC(OCC=4N=CC=NC=4)=CC=3)C2=C1 GWVYGWZSKXFUDP-UHFFFAOYSA-N 0.000 claims 1
- UVCJJKZUWSAMAE-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=CC(OCC=4N=CC=CC=4)=CC=3)C2=C1 UVCJJKZUWSAMAE-UHFFFAOYSA-N 0.000 claims 1
- NKHXKUSZNCCXTE-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-[(3-fluorophenyl)methoxy]-3-methoxyanilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical class C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC(OC)=C2OC1CCN(C(=O)CN(C)C)CC1 NKHXKUSZNCCXTE-UHFFFAOYSA-N 0.000 claims 1
- HFHOERMVRHCGBS-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-[(3-fluorophenyl)methoxy]-3-methoxyanilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(C(=O)CN(C)C)CC1 HFHOERMVRHCGBS-UHFFFAOYSA-N 0.000 claims 1
- JSVRRJAUFUTRCW-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-[(3-fluorophenyl)methoxy]anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 JSVRRJAUFUTRCW-UHFFFAOYSA-N 0.000 claims 1
- YOQLVJQTNWDMPQ-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-[(3-fluorophenyl)methoxy]anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=CC(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 YOQLVJQTNWDMPQ-UHFFFAOYSA-N 0.000 claims 1
- RPDPJGBITDCLOA-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[7-methoxy-4-[3-methoxy-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=NC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC(OC)=C2OC1CCN(C(=O)CN(C)C)CC1 RPDPJGBITDCLOA-UHFFFAOYSA-N 0.000 claims 1
- CRWGJNQMNWADKW-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[7-methoxy-4-[3-methoxy-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC(OC)=C2OC1CCN(C(=O)CN(C)C)CC1 CRWGJNQMNWADKW-UHFFFAOYSA-N 0.000 claims 1
- DNRBJKZGVVZPSC-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[7-methoxy-4-[4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1)=CC=C1OCC1=CN=CC=N1 DNRBJKZGVVZPSC-UHFFFAOYSA-N 0.000 claims 1
- JFIBRFHGXARFDL-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[7-methoxy-4-[4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1)=CC=C1OCC1=CC=CC=N1 JFIBRFHGXARFDL-UHFFFAOYSA-N 0.000 claims 1
- ALDKMUMLEZDDDX-UHFFFAOYSA-N 2-hydroxy-1-[3-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-6-yl]oxyazetidin-1-yl]ethanone Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC(C1=C2)=NC=NC1=CC=C2OC1CN(C(=O)CO)C1 ALDKMUMLEZDDDX-UHFFFAOYSA-N 0.000 claims 1
- WGVIMYSLSFIRNA-UHFFFAOYSA-N 2-hydroxy-1-[4-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(C(=O)CO)CC1 WGVIMYSLSFIRNA-UHFFFAOYSA-N 0.000 claims 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- GVTKSUVXHBZNTA-UHFFFAOYSA-N 6-(1-methylsulfonylpiperidin-4-yl)oxy-n-[4-(1,3-thiazol-2-ylsulfanyl)phenyl]quinazolin-4-amine Chemical compound C1CN(S(=O)(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=CC(SC=4SC=CN=4)=CC=3)C2=C1 GVTKSUVXHBZNTA-UHFFFAOYSA-N 0.000 claims 1
- FHQTVYVBVMWTPS-UHFFFAOYSA-N 7-methoxy-6-(1-methylsulfonylpiperidin-4-yl)oxy-n-[4-(1,3-thiazol-2-ylsulfanyl)phenyl]quinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC(C=C1)=CC=C1SC1=NC=CS1 FHQTVYVBVMWTPS-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 241000282412 Homo Species 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- FHVDJQINBGRTEQ-UHFFFAOYSA-N n-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical class CN1C=CN=C1SC(C(=C1)Cl)=CC=C1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(S(C)(=O)=O)CC1 FHVDJQINBGRTEQ-UHFFFAOYSA-N 0.000 claims 1
- BAGWNVXNHRKDRU-UHFFFAOYSA-N n-[3-chloro-4-(pyrazin-2-ylmethoxy)phenyl]-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C1CN(S(=O)(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)C2=C1 BAGWNVXNHRKDRU-UHFFFAOYSA-N 0.000 claims 1
- XUTCVYQECWOYIA-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C1CN(S(=O)(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 XUTCVYQECWOYIA-UHFFFAOYSA-N 0.000 claims 1
- GTAPRRNJTXVVRK-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-6-[(1-methylsulfonylpyrrolidin-3-yl)methoxy]quinazolin-4-amine Chemical compound C1N(S(=O)(=O)C)CCC1COC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 GTAPRRNJTXVVRK-UHFFFAOYSA-N 0.000 claims 1
- IIOUGCSKSQIEQD-UHFFFAOYSA-N n-[3-ethynyl-4-[(3-fluorophenyl)methoxy]phenyl]-7-methoxy-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC(C=C1C#C)=CC=C1OCC1=CC=CC(F)=C1 IIOUGCSKSQIEQD-UHFFFAOYSA-N 0.000 claims 1
- MQIAKRLIMWVTPK-UHFFFAOYSA-N n-[3-fluoro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical class CN1C=CN=C1SC(C(=C1)F)=CC=C1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(S(C)(=O)=O)CC1 MQIAKRLIMWVTPK-UHFFFAOYSA-N 0.000 claims 1
- QWVDAJRPQDDAEF-UHFFFAOYSA-N n-[3-fluoro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-7-methoxy-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC(C=C1F)=CC=C1SC1=NC=CN1C QWVDAJRPQDDAEF-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
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| Application Number | Priority Date | Filing Date | Title |
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| EP03292279 | 2003-09-16 | ||
| PCT/GB2004/003931 WO2005026151A1 (en) | 2003-09-16 | 2004-09-14 | Quinazoline derivatives as tyrosine kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
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| JP2007505873A5 true JP2007505873A5 (enExample) | 2007-11-01 |
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| EP (1) | EP1664028A1 (enExample) |
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| CN (1) | CN1882573A (enExample) |
| AU (1) | AU2004272350A1 (enExample) |
| BR (1) | BRPI0414447A (enExample) |
| CA (1) | CA2539022A1 (enExample) |
| IL (1) | IL174258A0 (enExample) |
| MX (1) | MXPA06002963A (enExample) |
| NO (1) | NO20061321L (enExample) |
| WO (1) | WO2005026151A1 (enExample) |
| ZA (1) | ZA200602190B (enExample) |
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| RU2004116911A (ru) * | 2001-11-03 | 2005-11-10 | Астразенека Аб (Se) | Производные хиназолина в качестве противоопухолевых средств |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005026150A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| BRPI0414488A (pt) * | 2003-09-16 | 2006-11-14 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, métodos para produzir um efeito anti - proliferativo em um animal de sangue quente, para prevenção ou tratamento de tumores em um aminal de sangue quente, para fornecer um efeito inibidor da tirosina quinase de egfr seletivo em um animal de sangue quente e para tratar um cáncer em um animal de sangue quente e, processo para a preparação de um derivado de quinazolina |
| WO2005026156A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| DE602004004811T2 (de) * | 2003-09-19 | 2007-11-22 | Astrazeneca Ab | Chinazolinderivate |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| ATE413389T1 (de) * | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
| ATE501148T1 (de) * | 2004-12-14 | 2011-03-15 | Astrazeneca Ab | Pyrazolopyrimidinverbindungen als antitumormittel |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508715D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| EP1904458A1 (de) * | 2005-07-04 | 2008-04-02 | Boehringer Ingelheim International GmbH | Verfahren zur herstellung von chinazolinonderivaten |
| US20100234371A1 (en) * | 2005-08-22 | 2010-09-16 | Frank Himmelsbach | Bicyclic heterocycles, pharmaceutical compositions containing these compounds, the use thereof and processes for the preparation thereof |
| WO2007034143A1 (en) * | 2005-09-20 | 2007-03-29 | Astrazeneca Ab | Quinazoline derivatives as anticancer agents |
| ES2354457T3 (es) * | 2005-09-20 | 2011-03-15 | Astrazeneca Ab | Compuestos de 4-(1h-indazol-5-il-amino)-quinazolina como inhibidores del receptor erbb de la tirosina quinasa para el tratamiento del cáncer. |
| DE602006021645D1 (de) | 2005-11-15 | 2011-06-09 | Array Biopharma Inc | Verfahren und Zwischenverbindungen zur Herstellung von N4-Phenyl-Quinazolin-4-Amin Derivaten |
| EP1957499A1 (en) * | 2005-12-02 | 2008-08-20 | AstraZeneca AB | 4-anilino-substituted quinazoline derivatives as tyrosine kinase inhibitors |
| CA2663436A1 (en) * | 2006-10-04 | 2008-04-10 | Pfizer Products Inc. | Pyrido[4,3-d]pyrimidin-4(3h)-one derivatives as calcium receptor antagonists |
| EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| JP5377332B2 (ja) | 2007-02-06 | 2013-12-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 二環式へテロ環、それらの化合物を含む薬剤、その使用及びその製法 |
| TWI377944B (en) * | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| WO2009098061A1 (de) | 2008-02-07 | 2009-08-13 | Boehringer Ingelheim International Gmbh | Spirocyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| MX2010012442A (es) | 2008-05-13 | 2011-10-11 | Astrazeneca Ab | Sal de fumarato de 4-(3-cloro-2-fluoroanilino)-7-metoxi-6-{[1-(n-m etilcarbamoilmetil) piperidin-4-il]oxi}quinazolina. |
| EP2313397B1 (de) | 2008-08-08 | 2016-04-20 | Boehringer Ingelheim International GmbH | Cyclohexyloxy-substituierte heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| US9168254B2 (en) | 2011-10-14 | 2015-10-27 | Array Biopharma Inc. | Polymorphs of ARRY-380, a selective HER 2 inhibitor and pharmaceutical compositions containing them |
| CN105153046A (zh) * | 2015-08-25 | 2015-12-16 | 佛山市赛维斯医药科技有限公司 | 双卤素取代的乙氧基苯并喹唑啉类酪氨酸激酶抑制剂及用途 |
| CN105153047A (zh) * | 2015-08-25 | 2015-12-16 | 佛山市赛维斯医药科技有限公司 | 含新型苯并喹唑啉和邻位氟结构的酪氨酸激酶抑制剂及用途 |
| UY37935A (es) * | 2017-10-18 | 2020-03-31 | Spectrum Pharmaceuticals Inc | Inhibidores de tirosina quinasas de la familia de los egfr mutantes |
| WO2020262998A1 (ko) * | 2019-06-26 | 2020-12-30 | 한미약품 주식회사 | 항 종양 활성을 갖는 신규 퀴나졸린 유도체 및 이를 포함하는 약학 조성물 |
| WO2021231400A1 (en) * | 2020-05-12 | 2021-11-18 | Accutar Biotechnology, Inc. | Bis-aryl ethers containing n-acyl azetidine as egfr/her2 inhibitors |
| CN115803326B (zh) * | 2020-11-23 | 2024-03-26 | 上海和誉生物医药科技有限公司 | Egfr抑制剂及其制备方法与在药学上的应用 |
| WO2022140769A1 (en) * | 2020-12-22 | 2022-06-30 | Enliven Therapeutics, Inc. | Lactam (hetero)arylfusedpyrimidine derivatives as inhibitors of erbb2 |
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| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| RU2004116911A (ru) * | 2001-11-03 | 2005-11-10 | Астразенека Аб (Se) | Производные хиназолина в качестве противоопухолевых средств |
| TW200813014A (en) * | 2002-03-28 | 2008-03-16 | Astrazeneca Ab | Quinazoline derivatives |
| NZ536114A (en) * | 2002-03-30 | 2007-11-30 | Boehringer Ingelheim Pharma | 4-(N-phenylamino)-quinazolines / quinolines as tyrosine kinase inhibitors |
| US6924285B2 (en) * | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| CA2533345A1 (en) * | 2003-07-29 | 2005-02-10 | Astrazeneca Ab | Piperidyl-quinazoline derivatives as tyrosine kinase inhibitors |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| WO2005026150A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| BRPI0414488A (pt) * | 2003-09-16 | 2006-11-14 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, métodos para produzir um efeito anti - proliferativo em um animal de sangue quente, para prevenção ou tratamento de tumores em um aminal de sangue quente, para fornecer um efeito inibidor da tirosina quinase de egfr seletivo em um animal de sangue quente e para tratar um cáncer em um animal de sangue quente e, processo para a preparação de um derivado de quinazolina |
| DE602004004811T2 (de) * | 2003-09-19 | 2007-11-22 | Astrazeneca Ab | Chinazolinderivate |
| MXPA06003341A (es) * | 2003-09-25 | 2006-06-08 | Astrazeneca Ab | Derivados de quinazolina. |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| ATE413389T1 (de) * | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
-
2004
- 2004-09-14 MX MXPA06002963A patent/MXPA06002963A/es unknown
- 2004-09-14 CN CNA2004800335692A patent/CN1882573A/zh active Pending
- 2004-09-14 JP JP2006526684A patent/JP2007505873A/ja active Pending
- 2004-09-14 AU AU2004272350A patent/AU2004272350A1/en not_active Abandoned
- 2004-09-14 BR BRPI0414447-3A patent/BRPI0414447A/pt not_active Application Discontinuation
- 2004-09-14 CA CA002539022A patent/CA2539022A1/en not_active Abandoned
- 2004-09-14 US US10/571,851 patent/US20070032508A1/en not_active Abandoned
- 2004-09-14 EP EP04768477A patent/EP1664028A1/en not_active Withdrawn
- 2004-09-14 WO PCT/GB2004/003931 patent/WO2005026151A1/en not_active Ceased
-
2006
- 2006-03-12 IL IL174258A patent/IL174258A0/en unknown
- 2006-03-15 ZA ZA200602190A patent/ZA200602190B/en unknown
- 2006-03-23 NO NO20061321A patent/NO20061321L/no not_active Application Discontinuation
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